Chania is a beautiful resort town with a long history, Crete, Greece

Greece Island Explorer: Crete, Naxos, Mykonos & More

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited


Places Visited

Mykonos, Delos, Chora, Naxos...

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Suggested Duration

14 Days

Explore and experience iconic beaches and enchanting panoramas during your 14-day Greece island-hopping vacation. You will travel to four islands known for their combination of pink and white beaches, whitewashed villages, and fascinating ancient ruins. Your tour will be custom-tailored to immerse you in Greece’s history and heritage as you traverse the marvels of Crete, Mykonos, Naxos, and Santorini for an unforgettable Mediterranean getaway.

Customizable Itinerary

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Trip Highlights

  • Relax on the expansive beaches of Naxos, an island that helps you escape the world
  • Indulge in the beauty of Santorini, an island that connects you to Greek tradition
  • Discover Ancient Greece on a day trip to Delos, the most important archaeological ruins outside Athens
  • Explore the contemporary chic of Mykonos, an island that’s all about the Greek vacation style
  • Walk across astonishing pink and white sands around the island of Crete, the island where beach time meets ambient neighborhoods
  • Gain an intimate understanding of the food, the tour including a household dinner in Mykonos and a cooking class on Naxos
  • Enjoy all the history, like Venetian harbors, iconic windmills, ancient temples, and small whitewashed villages
  • Cruise around Santorini on a catamaran, just one of the Aegean Sea highlights on this tour

Detailed Description

The highlight of the Greek islands is how each one feels completely different. Sure, you can look at photos of blue and white villages and imagine the islands are very similar. Or you can spend an evening in a taverna and think it’s quintessentially Greek, without initially noticing the island individualism. But when you get to know the country you experience its nuance. Mykonos and Naxos are neighbors but are absolutely distinct in atmosphere and style. Delos is all archaeological ruin while Santorini is dominated by the dramatic work of nature, and these islands are all in the Cyclades chain. When you travel to Crete, the changes are even more distinctive as if you are exploring a different country entirely.

It is this individualism and inimitability that has made Greek island hopping such a famous vacation experience. A short ferry west, and everything changes. A quick hop south, and there is a new collection of treasures to find. This two-week tour is handcrafted to incorporate four corners of the Greek experience with Mykonos, Naxos, Santorini, and Crete. These are not only the most diverse islands, but they are neatly connected on the ferry route south. Over the two weeks, you will take day trips to smaller islands, including the birthplace of Apollo – Naxos – and the breathtaking white sand of Elafonisi.

Fly to Mykonos, the most developed and contemporary of the islands. Chic cafes meet with swanky seafood restaurants and languid beaches. It is an island populated by jet-setters, less authentic than the others but packed with beautiful streets and sights. Spend three nights amid the bustle of Hora, easing into the sultry island atmosphere. On day two you have dinner at a small Mykonian country household while day three is dedicated to the ruins of Delos nearby. Mykonos is an incredibly easy first stop, and by day four you will be looking forward to something a little more traditional.

So enter Naxos, an undeveloped island with just a handful of boutique hotels. Walk to deserted, expansive beaches during the day, feeling the escapism that the Cyclades can provide. Sink your toes into cooling sand, feel the salty breeze through your hair and visit a handful of temple ruins devoid of tourists. Go on a Cyclades cooking class, and spend your evenings in tiny whitewashed villages that have not yet been populated by souvenir shops. Naxos is the unsung gem of the Cyclades, and after three days you will realize why people don’t like to shout too loudly about its riches, as some islands are best left as they always have been.

Take the ferry south to Santorini and the most photogenic of Greece’s islands. It has the quintessential Greek island image many people are expecting, where blue domes and window shutters enliven the whitewashed cubist villages. Think breathtaking sunsets, turquoise waters, swathes of vineyards and getting lost in the mazy villages. You will be staying in the largest village Oia, which is linked to Fira by a stunning walk along the old volcanic caldera. Enjoy an afternoon of catamaran cruising on day eight, stopping at caves and lagoon-like waters to swim. Then spend day nine in the vineyards and small villages, getting to know parts of Santorini that have not yet been popularized by Instagram.

Crete is an enormous island, comfortably larger than all the other previous three put together. Disembarking in Heraklion, you spend a day amid historical highlights, like a medieval old city and vast Mycenaean ruins. You spend four nights in Chania, a charming Venetian-styled harbor city that’s packed full of alleys and cobbles. From here you make excursions to the white sands of Elafonisi and pink sands of Balos, plus get guided through local neighborhoods that seem frozen in the 17th and 18th centuries. Chania is a relaxed yet exciting destination to end on, and when you need to be alone, there are some great beaches within easy reach. Consider learning more about our travelers’ best Greece vacation experiences by reading their Greece travel reviews.

Starting Price

$4,545 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

Reviews of Zicasso's Referral Service

4.93 stars based on 1857 reviews.

Greece Vacation Review: Crete, Chania, Santorini, Oia, Naxos,...
"We have traveled extensively and this was one of the best...

Reviewed By Mary E.

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"Our trip was meticulously planned and executed by Zicasso’s...

Reviewed By Lisa G.

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"We had a wonderful trip to Greece. All transport, tours,...

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"We had a great trip! When planning it, I felt like the...

Reviewed By Katherine D.

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"From the moment we arrived to the moment we left, we never...

Reviewed By Donna K.

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"Zicasso was very accessible to us throughout the planning...

Reviewed By Heidi F.

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